Record Information
Version1.0
Created at2020-03-19 00:46:25 UTC
Updated at2020-12-07 19:07:34 UTC
CannabisDB IDCDB000608
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFormic acid
DescriptionFormic acid, also known as methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced through the oxidation of methanol. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a by-product in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465 ). Formic acid has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
Synonyms
ValueSource
Acide formiqueChEBI
AmeisensaeureChEBI
Aminic acidChEBI
BilorinChEBI
Formylic acidChEBI
H-COOHChEBI
HCO2HChEBI
HCOOHChEBI
Hydrogen carboxylic acidChEBI
Methanoic acidChEBI
Methoic acidChEBI
AminateGenerator
FormylateGenerator
Hydrogen carboxylateGenerator
MethanoateGenerator
MethoateGenerator
FormateGenerator
Add-FHMDB
AmeisensaureHMDB
Collo-bueglattHMDB
Collo-didaxHMDB
FormiraHMDB
FormisotonHMDB
Methanoic acid monomerHMDB
MyrmicylHMDB
Sodium formateHMDB
SybestHMDB
Wonderbond hardener m 600lHMDB
Calcium formateHMDB
Cobalt(II) formate dihydrateHMDB
Formic acid, aluminum saltHMDB
Formic acid, copper saltHMDB
Formic acid, cromium (+3) saltHMDB
Lithium formateHMDB
Ammonium formateHMDB
Formic acid, ammonium (4:1) saltHMDB
Formic acid, ammonium saltHMDB
Formic acid, calcium saltHMDB
Formic acid, copper (+2) saltHMDB
Formic acid, lead (+2) saltHMDB
Formic acid, lead saltHMDB
Formic acid, nickel saltHMDB
Formic acid, potassium saltHMDB
Formic acid, strontium saltHMDB
MafusolHMDB
Ammonium tetraformateHMDB
Formic acid, 14C-labeledHMDB
Formic acid, cobalt (+2) saltHMDB
Formic acid, copper, ammonium saltHMDB
Formic acid, sodium saltHMDB
Formic acid, sodium salt, 14C-labeledHMDB
Formic acid, ammonium (2:1) saltHMDB
Formic acid, cadmium saltHMDB
Formic acid, cesium saltHMDB
Formic acid, copper, nickel saltHMDB
Formic acid, cromium (+3), sodium (4:1:1) saltHMDB
Formic acid, lithium saltHMDB
Formic acid, magnesium saltHMDB
Formic acid, nickel (+2) saltHMDB
Formic acid, rubidium saltHMDB
Formic acid, sodium salt, 13C-labeledHMDB
Formic acid, thallium (+1) saltHMDB
Formic acid, zinc saltHMDB
Nickel formate dihydrateHMDB
Aluminum formateHMDB
Potassium formateHMDB
Strontium formateHMDB
Lead formateHMDB
Nickel formateHMDB
Chromic formateHMDB
Cobaltous formateHMDB
Cupric formateHMDB
Magnesium formateHMDB
Zinc formateHMDB
Chemical FormulaCH2O2
Average Molecular Weight46.03
Monoisotopic Molecular Weight46.0055
IUPAC Nameformic acid
Traditional Nameformic acid
CAS Registry Number64-18-6
SMILES
OC=O
InChI Identifier
InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point8.4 °CNot Available
Boiling Point100.8 °CWikipedia
Water Solubility1000 mg/mLNot Available
logP-0.54HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.47ALOGPS
logP-0.27ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.15 m³·mol⁻¹ChemAxon
Polarizability3.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004j-9000000000-2e63b0c1e2e417b0d747Spectrum
Predicted GC-MSFormic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9000000000-5d27bb312e37a2c8994fSpectrum
Predicted GC-MSFormic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-9200000000-2a89ba98485194acd75aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0002-9000000000-a8fbddf8ca4197b30013Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-0002-9000000000-98310116f8a2d6a969ceSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-0002-9000000000-ec8753fd9790a3cf0be8Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0002-9000000000-121d1a025b72a70e412aSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0002-9000000000-5f1955dee7ab988e86ddSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0002-9000000000-f8e14272296ee06d19f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
S-formylglutathione hydrolaseESD13q14.1-q14.2P10768 details
AspartoacylaseASPA17p13.3P45381 details
Aspartoacylase-2ACY3Q96HD9 details
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD114q24P11586 details
GTP cyclohydrolase 1GCH114q22.1-q22.2P30793 details
Peptide deformylase, mitochondrialPDF16q22.1Q9HBH1 details
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1L6q25.1Q6UB35 details
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD22p13.1Q7Z650 details
Kynurenine formamidaseAFMID17q25.3Q63HM1 details
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A115q24.1A0N0X8 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
AspartoacylaseASPA17p13.3P45381 details
Aspartoacylase-2ACY3Q96HD9 details
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Peptide deformylase, mitochondrialPDF16q22.1Q9HBH1 details
Cytochrome P450 2E1CYP2E110q24.3-qterP05181 details
Cytochrome P450 3A43CYP3A437q21.1Q9HB55 details
Cytochrome P450 1B1CYP1B12p22.2Q16678 details
Cytochrome P450 2C18CYP2C1810q24P33260 details
Cytochrome P450 2F1CYP2F119q13.2P24903 details
Cytochrome P450 4X1CYP4X11Q8N118 details
Cytochrome P450 2B6CYP2B619q13.2P20813 details
Cytochrome P450 3A5CYP3A57q21.1P20815 details
Cytochrome P450 2A13CYP2A1319q13.2Q16696 details
Cytochrome P450 3A7CYP3A77q21-q22.1P24462 details
Cytochrome P450 4B1CYP4B11p34-p12P13584 details
Cytochrome P450 4Z1CYP4Z11p33Q86W10 details
Cytochrome P450 1A2CYP1A215q24.1P05177 details
Cytochrome P450 19A1CYP19A115q21.1P11511 details
Cytochrome P450 2C8CYP2C810q23.33P10632 details
Cytochrome P450 2S1CYP2S119q13.1Q96SQ9 details
Cytochrome P450 2J2CYP2J21p31.3-p31.2P51589 details
Cytochrome P450 2A7CYP2A719q13.2P20853 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A115q24.1A0N0X8 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000142
DrugBank IDDB01942
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012804
KNApSAcK IDC00001182
Chemspider IDNot Available
KEGG Compound IDC00058
BioCyc IDFORMATE
BiGG IDNot Available
Wikipedia LinkFormic_acid
METLIN IDNot Available
PubChem Compound284
PDB IDNot Available
ChEBI ID30751
References
General References
  1. Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. [PubMed:22292465 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 40 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Catalyzes the deacetylation of N-acetylaspartic acid (NAA) to produce acetate and L-aspartate. NAA occurs in high concentration in brain and its hydrolysis NAA plays a significant part in the maintenance of intact white matter. In other tissues it act as a scavenger of NAA from body fluids.
Gene Name:
ASPA
Uniprot ID:
P45381
Molecular weight:
35734.79
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Plays an important role in deacetylating mercapturic acids in kidney proximal tubules (By similarity).
Gene Name:
ACY3
Uniprot ID:
Q96HD9
Molecular weight:
Not Available
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
Not Available
Gene Name:
MTHFD1
Uniprot ID:
P11586
Molecular weight:
101530.36
General function:
Involved in GTP cyclohydrolase I activity
Specific function:
Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
Gene Name:
GCH1
Uniprot ID:
P30793
Molecular weight:
27902.855
General function:
Involved in iron ion binding
Specific function:
Removes the formyl group from the N-terminal Met of newly synthesized proteins (By similarity).
Gene Name:
PDF
Uniprot ID:
Q9HBH1
Molecular weight:
27013.25
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2 (By similarity).
Gene Name:
MTHFD1L
Uniprot ID:
Q6UB35
Molecular weight:
105888.19
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MTHFD2
Uniprot ID:
Q7Z650
Molecular weight:
26849.1
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5

Only showing the first 10 proteins. There are 40 proteins in total.